Buchwald–Hartwig amination, record ord-b45fc3e4fad4439cafccda47ed5c0991
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Methyl 5-bromo-2-iodobenzoate | C₈H₆BrIO₂ | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | Methyl 5-bromo-2-morpholinobenzoate | C₁₂H₁₄BrNO₃ | 17.85% |
Conditions
- Temperature
- 100 °C
Yield
- 18% of Methyl 5-bromo-2-morpholinobenzoate.
Procedure
Copied from the source record, unedited
To a solution of methyl 5-bromo-2-iodobenzoate (2.1 g, 6.16 mmol) in DME (15 mL) were morpholine (0.593 mL, 6.78 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.384 g, 0.62 mmol), Palladium acetate (0.138 g, 0.62 mmol) and CESIUM CARBONATE (2.81 g, 8.62 mmol) added. The mixture was heated in the microwave oven for 1h. The solvent was evaporated and the crude product was added to a silica gel column, 0-25% EtOAc in heptane yielding [Products]
The source
This record comes from experimental reaction archive (ord-b45fc3e4fad4439cafccda47ed5c0991). Open the source and check it against what is on this page.
experimental reaction archive record ord-b45fc3e4fad4439cafccda47ed5c0991 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.